Chief of Staff at Leap (New York, NY)Chief of Staff

Leap is one of the fastest-growing benefits solutions and a category-defining pioneer in employer specialty pharmacy. We are reshaping how life-changing therapies are delivered and financed, ensuring patients get the treatment they need while employers finally get a fair deal.

Specialty drugs and infusions represent nearly 10% of all healthcare spend and are the fastest-growing cost category for employers. Leap tackles this challenge with a novel approach: eliminating hidden markups, expanding access to high-quality infusion providers, and bringing clarity and fairness to how therapies are priced and paid for.

We’re proud to partner with numerous Fortune 500 companies and leading TPAs. Each patient we serve creates immediate ROI: lower costs, improved access, and better care. Join us as we redefine what’s possible in specialty care.

Leap Health is entering a defining phase of growth. As we move to double our team again in the next 12 months, the complexity of the business will increase exponentially. We are looking for a Chief of Staff to build the connective tissue that holds the organization together.

In this role, you will be an accelerator. Your primary mandate is to ensure information flows seamlessly across the organization so that leadership can make high-quality decisions quickly. You will own the rhythm of the business and tackle high-priority cross-functional projects that allow us to scale without stalling.

• Architect the "Rhythm of Business": You will own the cadence and preparation for our most critical operating meetings (Executive Team Weekly, Monthly all Hands, QBRs, Board Meetings). You ensure that every meeting has a clear agenda, the necessary data is prepped in advance, and that we leave with explicit decisions and owners.
• Maximize Decision Velocity: You will prevent decision paralysis by ensuring the CEO and Leadership Team have the right context at the right time. You will synthesize complex information from across the company into clear options and recommendations, ensuring no critical decision stalls due to lack of clarity.
• Lead Special Projects: You will act as the interim owner for high-priority initiatives that fall outside of existing departments (e.g., executing a new market entry analysis, leading a compliance overhaul, or operationalizing a new partnership).
• Drive Strategic Accountability (OKRs): You will manage our goal-setting process. You are the "scorekeeper" who tracks progress against our objectives, holding leaders accountable to their commitments and flagging deviations early.

• The "Integrator" Mindset: 5+ years of experience in BizOps, Strategy, or Consulting. You are skilled at connecting dots between disparate functions.
• Synthesis Skills: You can read a 20-page document or sit in a chaotic hour-long debate and distill it down to a one-page summary of the core issues and necessary next steps.
• Process, Not Bureaucracy: You know how to implement just enough process to create speed and clarity, without adding administrative bloat that slows us down.
• Healthcare/Tech Context: You understand that in health-tech, "move fast" must be balanced with clinical rigor. You can navigate complex stakeholder environments.
• Data-Driven: You are comfortable digging into the metrics. You don't just report the numbers; you understand what they mean for the business model.

At Leap, we’re building an outlier company with real impact — and that takes focus, energy, and commitment. If that excites you, we’d love to hear from you.

Leap is an equal opportunity employer and welcomes applicants from all backgrounds. We’re committed to building a team that reflects a diversity of perspectives, experiences, and identities.